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Chapter 22

Chapter 22

Problem 22-2
(a) 4 (b) 3 (c) 3 (d) 2 (e) 4 (f) 5
Problem 22-4
Acid-catalyzed formation of an enol is followed by deuteronation of the enol double bond and dedeuteronation of oxygen.
Problem 22-5
1. Br2; 2. Pyridine, heat
Problem 22-6
The intermediate α-bromo acid bromide undergoes a nucleophilic acyl substitution reaction with methanol to give an α-bromo ester.
Problem 22-7
(a)
CH3CH2CHO
(b)
(CH3)3CCOCH3
(c)
CH3CO2H
(d)
PhCONH2
(e)
CH3CH2CH2CN
(f)
CH3CON(CH3)2
Problem 22-9
Acid is regenerated, but base is used stoichiometrically.
Problem 22-10
(a)
1. Na+ −OEt; 2. PhCH2Br; 3. H3O+
(b)
1. Na+ −OEt; 2. CH3CH2CH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
(c)
1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. H3O+
Problem 22-11
Malonic ester has only two acidic hydrogens to be replaced.
Problem 22-12
1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
Problem 22-13
(a)
(CH3)2CHCH2Br
(b)
PhCH2CH2Br
Problem 22-14
None can be prepared.
Problem 22-15
1. 2 Na+ −OEt; 2. BrCH2CH2CH2CH2Br; 3. H3O+
Problem 22-16
(a)
Alkylate phenylacetone with CH3I
(b)
Alkylate pentanenitrile with CH3CH2I
(c)
Alkylate cyclohexanone with H2C ═ CHCH2Br
(d)
Alkylate cyclohexanone with excess CH3I
(e)
Alkylate C6H5COCH2CH3 with CH3I
(f)
Alkylate methyl 3-methylbutanoate with CH3CH2I